Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method for R-6-hydroxy-1-aminoindan

A technology of aminoindane and R-6-, which is applied in the field of separation and preparation of optical pure chiral compounds, can solve the problems of separation and preparation of R-6-hydroxyl-1-aminoindene, etc., and achieve complete utilization of raw materials, optical The effect of high purity and simple operation

Active Publication Date: 2015-12-23
陈永军
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be found through the research literature that there is no information about how to use kinetics and dynamic kinetics to resolve and prepare R-6-hydroxyl-1-aminoindan

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method for R-6-hydroxy-1-aminoindan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] 1. Resolution of 6-hydroxy-1-aminoindan

[0009] In a 1000ML autoclave, add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 90.2g R-1-styryl acetate, 6g Candida antarctica lipase B and 10g Raney nickel, seal the autoclave , replace the air in the autoclave with nitrogen, and then pass hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and raise the temperature to 50°C for reaction; after 18 hours, take a sample to detect that 6-hydroxy-1-aminoindane is completely Converted to the acetyl compound of R-6-hydroxyl-1-aminoindan; after the reaction, the solution was concentrated and subjected to column chromatography to obtain 90.2 g of the pure R-6-hydroxyl-1-aminoindan acetyl compound , the yield is 95.5%.

[0010] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan salt

[0011] Take 95.5 g of the acetyl compound of R-6-hydroxy-1-aminoindane obtained by repeating the previous step several times and add it to 1000 ml of ethanol and concentrated hydrochlor...

Embodiment 2

[0015] 1. Resolution of 6-hydroxy-1-aminoindan

[0016] In a 1000ML autoclave, add 500ML n-hexane, 74.5G 6-hydroxy-1-aminoindan, 100g R-1-styroyl acetate, 7g Candida plicata lipase and 14g Raney nickel in sequence, and seal the autoclave , replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.5MP, start stirring, and raise the temperature to 40°C for reaction; after 15 hours, take a sample for detection, 6-hydroxy-1-aminoindane Completely converted into the acetyl compound of R-6-hydroxyl-1-aminoindan; after the reaction, the solution was concentrated and subjected to column chromatography to obtain 91.8g of the acetyl compound of R-6-hydroxyl-1-aminoindan , the yield is 96.1%.

[0017] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan salt

[0018] Take 95.5 g of the acetyl compound of R-6-hydroxy-1-aminoindane obtained by repeating the previous step several times and add it to a solution mixed with 1000 ml of ethanol a...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing R-6-hydroxy-1-aminoindan through biocatalytic dynamic kinetic resolution. The method comprises the following concrete steps: in an autoclave, allowing Candida antarctica Lipase B to catalyze transesterification reaction of 6-hydroxy-1-aminoindan with R-1-styracitol acetate so as to produce an R-6-hydroxy-1-aminoindan acyl compound and introducing Raney nickel as a racemization catalyst at the same time so as to guarantee complete conversion of 6-hydroxy-1-aminoindan into R-6-hydroxy-1-aminoindan; and hydrolyzing the obtained acyl compound so as to obtain R-6-hydroxy-1-aminoindan with an ee value of more than 99%. The method is simple to operate; raw materials are completely utilized; prepared R-6-hydroxy-1-aminoindan has high optical purity; and the method has great guidance and application values in production and preparation of R-6-hydroxy-1-aminoindan.

Description

technical field [0001] The invention relates to a method for the resolution and preparation of optically pure chiral compounds, in particular to a method for the preparation of R-6-hydroxyl-1-aminoindan by dynamic kinetic resolution. Background technique [0002] R-6-hydroxy-1-aminoindan as a chiral intermediate. In the existing related research, there are few reports on how to prepare optically pure R-6-hydroxy-1-aminoindan. It can be found through the research literature that there is no information on how to prepare R-6-hydroxyl-1-aminoindan by kinetic and dynamic kinetic resolution. The present invention uses Candida antarctica lipase B as the resolution catalyst, Raney nickel as the racemization catalyst, and successfully realizes dynamic kinetic resolution to prepare R- 6-hydroxyl-1-aminoindan, and the final product has good yield and high purity. Contents of the invention [0003] In order to solve the above problems, the present invention proposes dynamic kineti...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00C07C211/42C07C209/62
Inventor 陈永军
Owner 陈永军
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com